Michael Novogratz was in a good mood. It was the thirtieth reunion of Princeton’s class of 1987, and the on-again, off-again billionaire was getting a lot of respect. “I want to hit you up about something,” a two-star general said. “Those are the freshest kicks,” a young bro in a dressing gown observed, complimenting Novogratz’s black patent shoes with orange piping and matching tassels. (“It’s all about peacocking,” Novogratz later told me, of his sartorial extravagance.) He huddled with Joseph Lubin, a former roommate and one of the co-founders of the hit cryptocurrency platform Ethereum. It was a warm June day, last year, and the Princetonians were amiably crushing cans of Bud amid chants of “Tiger, tiger, tiger, sis sis sis, boom boom boom, ah!”

The alumni parade, known as the P-rade, started to wind through the neo-Gothic campus, its mob of participants marching past signs for a symposium entitled “Can America Still Lead?” As we joined the P-rade, we heard shouts of “Novo! Novo! Novo!” He stopped by a gaggle of young wrestlers, all of whom seemed monumentally drunker than the rest of Princeton’s population—a notable distinction. Novogratz, formerly the captain of the college’s wrestling team, slapped a half-naked man on the back so hard that he left a red palm print. “I five-starred a guy!” he shouted as we continued down the P-rade, men running up to him as if he were the mayor of a small Sicilian hill town. “Mr. Novogratz! I’m Goldman corporate trading!”

Princeton, like Wall Street, where Novogratz has made at least three fortunes and lost at least two, is full of stories about him. There was the story of how Novogratz never showed up for R.O.T.C. (he was admitted to Princeton on an R.O.T.C. scholarship). And the time, at the previous reunion, when he flew a helicopter—Novogratz did a year’s worth of helicopter-pilot training, at the Army’s flight school in Alabama—down Prospect Avenue, nearly clipping a gate. “He’s bombastic and he’s full of shit,” one of his friends said, “but he doesn’t have a mean bone in his body.” Novogratz, who is properly bald, with a pair of sharp blue eyes and a gravelly voice that can go full Muppet after a volley of drinks, was, uncharacteristically, sober. At the behest of his wife, he was preparing himself for an eleven-day Vipassana meditation retreat in Wales. “I’m trying to regrow my discipline muscle,” he told me as we approached the Tudor hulk of the Tiger Inn, his eating club, where a beer-pong tournament was already well under way in the basement.

Novogratz had risen quickly, at Goldman Sachs and in the hedge-fund world, but each rise was met with a stunning, often humiliating reversal—first a parting with Goldman, in 2000, over what has been referred to in the press as “lifestyle issues,” and then the removal from his partnership, in 2015, at the high-flying Fortress Group after losing a series of currency bets. Once worth north of two billion dollars, Novogratz had been reduced to the ranks of mere centimillionaires. But 2017 was proving to be pivotal for him and a motley band of other sidelined investors seeking redemption—think the Winklevoss twins—as they tethered themselves to the year’s most befuddling financial event: the rise of cryptocurrency.

Novogratz had recognized its potential when one of his partners at Fortress, Peter Briger, introduced him to one of its earlier evangelists, an Argentinean investor named Wences Casares. In 2013, Novogratz put seven million dollars of his own money in cryptocurrency investments when bitcoin was selling at around a hundred dollars a coin. (A single coin currently sells for more than sixty times that amount.) Citing his luck at being in the right place at the right time, Novogratz has called himself “the Forrest Gump of bitcoin.”

Novogratz’s crypto bets had coaxed him out of self-imposed retirement, and soon sprang him back onto CNBC and Bloomberg. Late last year, as the G.O.P.’s tax bill barrelled through Congress, he called Steve Mnuchin, the Treasury Secretary, an “idiot” (spelling out the word, for good measure) and rebuked Trump’s economic adviser Gary Cohn for the tax overhaul, saying that he “shouldn’t be able to live with himself.” Both Mnuchin and Cohn had been partners alongside Novogratz at Goldman Sachs, and this made for an unusual breach of Goldman etiquette.

To cap off the reunion, Novogratz had paid for a concert by Duran Duran. “Every five years, he does us well,” a classmate told me. Even in the middle of a streak of sobriety, it was hard for Novogratz to say no to a good party. “We’re a family of near-alcoholics,” he joked earlier that day, referring to the hungover crowd at a Princeton brunch that included his wife, Sukey Cáceres, also an alum, and their four children, three of whom have attended the university. The night ended with a touch of eighties style and contemporary dissonance. As gracefully aging Princetonians drained the booze from their red plastic cups, Simon Le Bon, dressed in what looked like a swath of green vinyl, belted out “A View to a Kill,” and, in one corner, Ted Cruz (class of ’92) darkly made his presence known.

In the past decade, a large number of the friends I had come of age with in Manhattan left the city, displaced by rising costs to Berlin or Los Angeles or the mid-Hudson Valley. These friends, many of whom were fellow-alumni of my alma maters, Stuyvesant High School and Oberlin College, were writers, graphic designers, architects, academics, and journalists—the heart of what used to be the creative middle class. As I walked down the now unfamiliar streets of my city, eying a new breed of closely cropped, athletic individuals, I kept wondering, Who are these people? Eventually, I discovered that they worked mostly for banks or hedge funds or private-equity firms. Around 2012, I decided that my next novel would be about finance. When I first broached the idea of making a fund manager the hero to a friend whose husband works in the industry, she asked me, “Why would you do that? Bankers have no imagination.” (In my research, wives saying unflattering things about their spouses became a consistent theme.)

Do bankers have imagination? That statement felt both like a challenge and like a lodestar for my work. I would find hedge funders worth writing about or invent my own. More than a few reminded me of Novogratz’s wrestling friends—scrappy lower-middle-class kids from the peripheries of New York or Naples or Moscow. As a hungry, insecure kid growing up in eastern Queens, I remember watching the movie “Wall Street” and fantasizing about how I would look in suspenders and a contrasting collar. The men on the big screen did not have to understand themselves; the money made them understood. Although my greed had been expunged at Oberlin, and the financial crisis of 2007-08 had left me with a more or less permanent view of finance as an industry built on fraud, I found it hard to dislike some of my new acquaintances. The more intellectually vibrant ones came with backgrounds in advanced math and physics; they approached their trades like a puzzle, albeit one they were increasingly unable to solve. Others seemed to be flirting with the edges of sociopathy, or, at least, an inability to pass “Blade Runner” ’s Voight-Kampff empathy test.

In the popular imagination, “hedge funder” has become shorthand for a special breed of super-rich, super-intelligent scoundrel. Hedge funds raise money from so-called accredited individuals (a minimum of a million dollars in investable assets is required) and institutions such as university endowments or pension and sovereign wealth funds, and then deploy it in any way they see fit. It may help to think of hedge-fund managers as an army of men—and they are mostly men—walking down the street with dustbusters, trying to suck up cash and assets from every nook and cranny in the universe. In theory, at least, hedge funds are supposed to generate returns in bear as well as bull markets, because the contents of their dustbusters are hedged, by the managers taking long positions on assets that are expected to increase in value and shorting those they expect will decrease.

The rise of this less regulated “buy” side of finance has put to shame the income of the “sell” side. Around Manhattan, “investment banker” now carries the same sad also-ran cachet as “doctor” or “lawyer.” An older managing director at a large bank complained of the struggles of the middle class. When I asked him to define “middle class,” he spoke of people like him, earning between two and four million dollars a year. Young analysts told me they were being priced out of Brooklyn, much less Manhattan, by rising hedge-fund plutocrats and their ilk.

Part of this may be ascribed to a strategy involving two numbers—“the two and twenty.” Traditionally, many hedge-fund managers have collected twenty per cent of a fund’s profits, and they have also kept two per cent of the assets committed to a fund, regardless of the outcome of their bets. Huge losses for clients could still mean a payday for managers. Wall Street has long been a place of outsized compensation for the few who can master its rules, or at least pretend to. (There is a book that handily explains the investor-manager relationship in its title alone: “Where Are the Customers’ Yachts?”) Hedge funds seemed to offer the best and the brightest the quickest road to riches yet. As one hedge-fund manager told me, “There’s money sloshing around and chunks falling off, and people get compensated for standing there.”

These people could be divided into many categories, but the two most useful I’ve found are the rainmakers—the polished, fraternal, athletically built avatars of the Princeton-Colgate-Duke axis—and the Dockers-wearing, kielbasa-munching math whizzes. Some funds seemed to make an art form out of how many brilliant physicists from the former Soviet Union can be squeezed into a small, overlit room. There was no question which of these two groups the socially brilliant but algorithmically challenged Novogratz belonged to.

What struck me about both sets was their desire to live their lives as a competitive sport. “Money has nothing to do with it,” Turney Duff, a former partner at a health-care hedge fund, told me. “It’s literally about winning.” I began to think of the financial world as a tax on the rest of us, a way to transfer wealth into the hands of a select few through their own considerable cleverness and also through the way their income was taxed versus our own.

And yet the majority of the hedge funders I befriended were not living happier or more interesting lives than my friends who had been exiled from the city. They had devoted their intellects and energies to winning a game that seemed only to diminish the players. One book I was often told to read was “Reminiscences of a Stock Operator,” first published in 1923. Written by Edwin Lefèvre, the novel follows a stockbroker named Lawrence Livingston, widely believed to be based on Jesse Livermore, a colorful speculator who rose from the era of street-corner bucket shops. I was astounded by how little had changed between the days of ticker tape and our own world of derivatives and flash trading, but a facet that none of the book’s Wall Street fans had mentioned was the miserableness of its protagonist. Livingston dreams of fishing off the Florida coast, preferably in his new yacht, but he keeps tacking back up to New York for one more trade. “Trading is addictive,” Novogratz told me at the Princeton reunion. “All these guys get addicted.” Livermore fatally shot himself in New York’s Sherry-Netherland Hotel in 1940.

By 2016, I started drinking more heavily than is usual for me (I was born in Russia). For the second year in a row, there were more shuttered hedge funds than new ones, investors having been turned off by a mixture of high fees and subpar returns, owing in part to a crowded field of funds executing similar strategies and also to an unusual absence of volatility in the markets. Even the legendary traders, like Paul Tudor Jones II, of Tudor Investment, were being walloped. The “two and twenty” model was turning into more of a “1.5 and fifteen” one. The secret-sauce bottles containing trading algorithms and the like had run empty, and to fill the void my new friends and I turned to Scotch—thirty-year-old Balvenie and twenty-one-year-old Hibiki. After a particularly rough night, my wife found me at 4 A.M., sitting in the corner of our bedroom, trying, and failing, to unbutton my shirt. The stress and the consequent loss of control felt familiar. The fund managers’ ambition was like a drug whose potency I had forgotten. At Stuyvesant High School, a competitive math-and-science school in Manhattan with a high proportion of first-generation immigrants, my classmates and I would get up every morning to wage battle over a hundredth of a percentile on our grade-point average; my new friends were fighting over so many basis points on their Bloomberg monitors. When we failed, we failed in front of our families, our ancestors, our future and our past.

Novogratz ran his first quasi hedge fund when he was barely four years old. The Novogratzes were a military family; in the late nineteen-sixties, they found themselves in Torrance, California. Novogratz and his older brother, Robert, went door-to-door in their neighborhood selling leaves, a useless commodity, to neighbors, five cents for yellow ones, ten for red ones. Robert was shy and hung back, but Michael would run up and ring the doorbell. The neighbors would ask him why the red ones were ten cents, and, according to his mother, Barbara, he would answer, “Look around—there are hardly any red leaves.” He had mastered the concept of supply and demand, not to mention the difference between two asset classes. When I mentioned this incident to Novogratz, he laughed, quickly seeing the parallel between his childhood enterprise and his current bet on cryptocurrency, which, like red leaves, relies on a tricky—some would say, imaginary—valuation. “It could be bitcoins,” he said.

Novogratz is the third of seven children, and his charm and his skills as a storyteller are tied to his membership in this brood of hyper-successful siblings. (Robert is a designer; his older sister Jacqueline is the founder of Acumen, a global venture firm; the younger siblings include a Wall Street salesman, a sports manager, the co-founder of a sustainable-agriculture investment fund, and a writer.) When I talked to Novogratz’s brothers and sisters, they all brought up the image of seven children growing up in a house with one bathroom, and living chiefly off their father’s modest government salary. There was also some version of “Our mother raised us like we were the Kennedys.”

Nowadays, Barbara Novogratz and Robert, Sr., who retired as a colonel after a long Army career, spend their winters in Virginia, where Novogratz attended high school, and their summers on Long Island, where he bought them a home near an estate he owns in Amagansett. Robert’s father was an immigrant from Austria. Lacking English skills, he settled in Pennsylvania, where he worked at a cement mill. “Dirty work,” Robert told me. Barbara grew up in Queens, in an Irish-German family. Her father died when she was young and her mother worked long hours as an accountant and a singer to make ends meet.

When Novogratz was twenty-five, he was set up on a blind date with Dora Cáceres, who goes by the nickname Sukey. She was in many ways his opposite—a budding intellectual, interested in semiotics, film theory, and the teachings of Ram Dass. Her parents were from Puerto Rico and had moved to the mainland before she was born.

I met Sukey in her office, which is downstairs from the Novogratzes’ palatial apartment, in Tribeca, and decorated with pachyderms in every form and material possible—“The elephant is my power animal,” she said. During our conversation, she told me about a horrific gang rape she suffered before she entered Princeton. The perpetrators walked free. The experience, in part, led to a life of seeking and, later on, of meditation. (Her book on meditation, “Just Sit,” co-written with Novogratz’s younger sister Beth, came out in December.) Conscripting Novogratz into her spiritual journey was one unlikely outcome of a marriage in which she described her husband as having come from the “privileged white male” baby-boomer generation and “bro culture.”

At the reunion, Novogratz’s friends referred to fearlessness as his best quality. When I asked them if there was anything he did fear, one woman said, “Ask Sukey.” Sukey brought up his parents, making sure to note how much they’ve grown (his father “recently became a vegetarian”). But, in describing Novogratz’s inability to fully connect with her during periods of their marriage, his occasional outbursts of rage over insignificant events (the loss of a jar of foreign currency, for example), and his difficulty in dealing with “the smacks in life,” such as his ouster from Fortress, she said, “Barbara and Bob loved him, but yet they love a winner.”

When I mentioned this to Novogratz, he said, “My mother told everyone I was going to be a senator.” Barbara, when asked, said that she thought he could have been President.

Novogratz started his career at Goldman Sachs as a lowly money-market salesman. It was right around April Fool’s Day, 1989, and he had just spent a year flying helicopters in Alabama. (He continued to serve in the New Jersey National Guard during his first years at Goldman.) The firm moved him to Tokyo, to sell Japanese government bonds to U.S. investors, and, after he expressed his unhappiness over the fact that traders usually made much more than salesmen, Jon Corzine, who was the co-head of the fixed-income division at the time, sent him to Hong Kong, in 1993, where, eventually, he ran the firm’s trading desk. Novogratz’s transition from salesman to trader may be the most salient fact of his career. There is a gulf of difference between the salesman’s ability to schmooze and charm and the trader’s ability to synthesize information about markets and make bets worth hundreds of millions of dollars. “I sometimes think that I was such a good bullshitter as a sales guy that Corzine decided to put me in the job where you couldn’t bullshit,” Novogratz once said, in an interview with Matthias Knab, of Opalesque TV. “The one thing about being a macro trader is that the P. & L. doesn’t lie at the end of the day and there was a real discipline needed.”

Macro funds look for broad social, political, and macroeconomic trends and, in effect, bet on the way they might affect financial markets. They execute trades using equities, bonds, currencies, commodities, and futures. Macro trading is essentially hubris. It is taking on the mantle of a short-term prophet, the Nostradamus of two months (or weeks or days or hours or minutes) from now, and predicting the shape of the world at that instant.

Some of Novogratz’s fellow hedge funders have questioned his grasp of the finer details of his trading strategies. “He acts like a visionary, but at heart he’s still a salesman,” one manager told me. Others dispute that view. “Mike always gave the most lucid, detailed, and compelling explanations of what was going on,” Peter Rose, who worked with Novogratz in Hong Kong, wrote to me. “He had an uncanny ability to see patterns, causes and effects, the butterfly moving its wings in Tokyo and the tsunami in Singapore and what was the connection, where others only saw chaos.” When the Asian financial crisis hit with full force, in 1997, Novogratz survived what Rose called “a nuclear shitstorm.” Novogratz, who successfully shorted the Thai baht, told me, “When Asia blew up, my team made a fortune.”

He has credited his success to his faith in intuition and has said of unsuccessful traders, “They’re bullish but they’re too scared to buy.” Goldman is notorious for its brutal “up or out” culture, but Novogratz thrived in it. He was made partner in 1998. In May, 1999, Goldman went public, entitling Novogratz to shares in the firm, and in December he was named president of Goldman Sachs Latin America, based in São Paulo. He never made it there.

What happened next is one of the most confusing parts of Novogratz’s career. When I brought it up, he reached for a fidget spinner. The year after Goldman Sachs went public, he left the firm. Widely regarded as one of Wall Street’s hardest-charging party animals, Novogratz cited his separation agreement with Goldman to explain why he could not talk at length about what took place, but summarized the nature of his downfall as the consequence of “partying like a rock star.”

“I felt, like, What the fuck did I do to my life?” he said. “What the fuck did I do to my family?”

Sukey Novogratz described the years the family spent in Asia as “very challenging for marriage.” Back then, her husband, she said, was “someone who was constantly hedging his bets, literally, in work and in life, like, eh, I can never fully commit, even though we were married.”

“It was a humiliating exit,” Novogratz said. “Period.” He went to rehab in Arizona to work on himself and his marriage. “I took it stone-cold serious. I’d never had a therapist in my life and since then I’ve had five.” Around that time, he ran six marathons in the Sahara desert over the course of six days. “That brought me back to life in a lot of ways.”

Scandals have a short half-life on Wall Street. In only a few years, Novogratz engineered his comeback, as a partner at Fortress Investments. With the arrival of Novogratz, along with Peter Briger, who had been a specialist in distressed debt, among other things, at Goldman, the new entity, which had been founded in 1998 as a private-equity company by a former partner at BlackRock and two former managing directors of U.B.S., expanded into the world of real estate, debt securities, and hedge funds. The vision for the firm, Novogratz said, was to be the Goldman Sachs of the “alternative management business.” Novogratz’s hedge fund was to focus on macro trading on a worldwide scale. In an interview during his time at Fortress, Novogratz said, “The assets we trade are big stories, the macroeconomic stories of the world. Global imbalances, business cycles. Will the euro survive? Will the Chinese growth model change?”

For Novogratz, macro trading relies on one’s ability to combine intuition with a mind-boggling number of data points prepared by researchers and analysts. “You see the ballet in the chart,” as he puts it. “We call it luck because we don’t have a word for it,” he told me. “It’s a different type of intelligence. It’s pattern recognition. Most great guys at macro, if you put a jar of jelly beans on the table they can outguess you.”

From 2002 to 2007, Novogratz’s hedge fund reached almost nine billion dollars in assets. In 2007, Fortress went public, creating wealth for its partners but also making them answerable to shareholders. “We were the only company, I think to this day, where five guys became billionaires in a day,” Novogratz said. With a net worth of $2.3 billion, a new vista of power and connection opened up for a man still in his early forties. Forbes put him at No. 407 on its list of the world’s billionaires.

Novogratz was a whiz at raising capital, but Fortress, like much of the financial world, was soon blindsided by the 2008 bankruptcy of Lehman Brothers and the ensuing crisis. “I saw it happening,” Novogratz said. “But I couldn’t move the ship fast enough.” He added, “With hindsight, macro shouldn’t be in a public company.” According to him, Lehman’s collapse alone cost the fund between four and five hundred million dollars. An acquaintance of Novogratz’s described running into him outside the offices of Fortress during that time, eating a hot dog as he braced for a meeting with his co-workers. “He says, ‘I don’t want to go up there. It’s all bad up there.’ The world was melting. He was very emotional.”

Novogratz’s fund eventually recovered. The lessons of the financial debacle were not universally learned on Wall Street, however. “Beginning in March, 2009, generally, the faster and more enthusiastically you embraced risk assets, the better you did,” Mary Childs, who has covered hedge funds and credit markets for almost a decade and is currently a senior reporter at Barron’s, told me. “If we were supposed to learn our lesson about risktaking, we didn’t.”

In 2015, after losing a bet of more than a hundred and fifty million dollars on the Swiss franc, Novogratz and his colleagues made the second of two huge bets that Brazilian interest rates would fall. The first had rested on the assumption that Dilma Rousseff, the President, would lose her reëlection bid, that she would be replaced by a leader who would be tougher on inflation, and that interest rates would fall as a result. In 2014, Novogratz predicted that this sequence of events would lead to “a major rally in Brazilian assets,” and, consequently, a windfall for Fortress. Instead, Rousseff won the election. The second bet relied on the belief that rates would fall as a result of the central bank’s actions. They didn’t. Rousseff was eventually impeached, and interest rates did fall after the new President took over, but, according to Novogratz, “it was too late for me.”

Fortress’s macro fund shut down in 2015 and Novogratz left the company. Investors lost between seven and fifteen per cent of their assets, depending on their share class. After he and Goldman parted ways, in 2000, Novogratz had described himself to the acquaintance who later ran into him eating the hot dog as a “discredited rich guy.” Now he was twice discredited, but the “rich” part certainly stuck, even after the Fortress fiasco. Novogratz’s shares were bought back by Fortress for approximately two hundred and fifty million dollars. (“In what other business can you blow yourself up, and still raise five hundred million for the next fund?” the ex-hedge funder, and now writer, Turney Duff once asked me.)

The loss of his partnership hurt on a personal as well as a financial level. If there was a single larger-than-life personality who inspired Novogratz as a child, it was his uncle Ed, a tax collector and a lover of jazz. “My dad was a quiet, tough guy,” he told me, “But his brother had the personality. He loved Wall Street gambling. The last words my uncle ever said to me: ‘Michael, what the hell is going on? I just got the new Forbes and you’re falling like a stone.’ He died thirty minutes later.”

According to Novogratz, cryptocurrencies were a direct result of the 2008 crisis, when people lost faith in banks and bankers. He talks about this with the ardor of a true believer. “I call it the decentralized revolution,” he said. “We don’t trust institutions, we don’t trust authority.” Bitcoin was launched in 2009 as a peer-to-peer-based currency, which allowed users to carry out payment transactions without an intermediary, like a bank or a credit-card company, while maintaining anonymity. The identity of Bitcoin’s founder, Satoshi Nakamoto—and whether the name represents an individual or a group of people—remains unknown.

After the collapse of his Fortress fund, Novogratz found himself on the coast of the Bay of Bengal in India, talking to his guru, Krishnaji, at the One World Academy, trying to figure out what to do with his life. (Tony Robbins connected the two men in 2007, and the meditation academy has many adherents from the worlds of finance and entertainment.) “What’s your vision now?” Krishnaji asked him. “What’s your purpose now?” According to Krishnaji, Novogratz’s answers vacillated between trying out a political career and giving finance another go. Back in Manhattan, the vision, aided by bitcoin, turned out to be finance again.

During the first dot-com bubble, the technology behind the boom and its subsequent bust was at least understood: you went on Pets.com and bought your dog a leash, which would then be delivered to you. Cryptocurrencies cannot be held or understood in any physical way; they have no central location, and this gives them, and their acolytes—Reddit libertarians, for example—an air of a religious experience. Novogratz told me, of a panel on crypto at which he spoke, “I got off the stage, some girl came up to me, she started, like, quaking, just wanted to tell me it was, like, life-changing for her. That the whole speech was. And then the Chinese wanted selfies, and then the Orthodox Jews wanted selfies. I must have done twenty selfies.”

Fiat currencies such as the dollar are backed by both central governments and their users, but cryptocurrencies are almost always backed by nothing more than their users. From bitcoin’s inception, production of the currency was limited by Satoshi Nakamoto to a maximum of twenty-one million coins, insuring eventual scarcity. A few holders of bitcoin and other cryptocurrencies have earned (or “mined,” as the terminology goes) their coins by providing the computing power that enables and verifies transactions in the network. Other holders have purchased them. Currency exchanges such as Coinbase, headquartered in San Francisco, allow anyone to buy a coin or a fraction of a coin for either fiat or cryptocurrencies, thus opening up the market to new users. The opaque universe in which the coins move, in conjunction with widespread uncertainty regarding future regulation—and the future of the crypto market itself—have created speculation and almost unheard of amounts of volatility. Some cryptocurrency pump-and-dump and pyramid schemes have resulted in Bernie Madoff-like levels of fraud. Wide-scale legitimate uses for the currency have proved elusive, and many now see bitcoin as a store of value rather than something with which you can buy a cheesesteak or pay for a manicure. There is also an environmental cost, a byproduct of the amount of computing power it can take to mine cryptocurrencies.

But that hasn’t stopped the crypto boom. Initial coin offerings, a form of crowdfunding, carry on apace. Companies on the verge of irrelevance, such as Kodak, are planning to mint their own currency (KodakCoin), as is the government of Venezuela (the petro).

The underlying technology is the blockchain system—a decentralized, algorithm-generated, regularly updated database distributed across a network of computers. What can you do with blockchain beyond buying drugs on the dark Web? Potentially, quite a lot. A ledger kept among a vast number of computers can transfer money more securely than traditional banks, and, possibly, faster, all the while denying Wells Fargo, say, a cut of the transaction. But that is only the start. Ethereum’s platform, for example, can work as a lawyer-free contract database dealing with everything from property sales to estate transfers.

Novogratz has certainly been making the most of the speculative bubble to rebuild his fortune, but he claims to be invested in the utopian aspects of blockchain as well. He doesn’t think that cryptocurrencies will replace the dollar or the yen, but he believes that they will be a boon to countries in the developing world, where people don’t have trust in their fiat currencies, and that blockchain can revolutionize the way information is logged and shared and, in our age of data breaches, protected. “I’m good at selling the dream,” he said. “I can get onstage and get people to start saying ‘Hallelujah! Hallelujah!’ ”

Novogratz’s enthusiasm is genuine and contagious. Then again, Twitter and Facebook were supposed to usher in a new era of democracy and transparency.

When I next saw Novogratz, in July of 2017, about a month after the Princeton reunion, he had recently returned from his Vipassana retreat. “This is not my normal vacation,” he told me, over a lunch at the Mercer Kitchen, in SoHo, a few blocks from his office, on Grand Street. “They put you into noble silence. You can’t lie, because you can’t talk. No thumbs-upping, no sign language. No sexual activity, including masturbation. It’s all self-monitoring.”

By the time he left the retreat, the lack of self-love and of communication with others seemed to have paid off on a grand karmic scale. Most of Novogratz’s profits had stemmed from his initial seven-million-dollar investment in 2013. “The ‘genius,’ if there was any, was riding the bet and switching,” Novogratz told me on another occasion, explaining that in early 2016 he had also bought Ethereum currency at around a dollar a coin, called an ether. Now he was toggling back and forth among various currencies, trying to minimize his risk as his fortune increased dramatically.

The price of ether had spiked during his meditation. “I got out,” he said, “and things had gone from two-fifty to three-fifty. I was, like, O.K., I just made a zillion dollars meditating. I should probably make two hundred million on this whole thing.” He cashed out some of his cryptocurrency to buy a G550 jet, a seaplane, and a Georg Baselitz sculpture. “For the first time, I kind of spoiled myself.”

The intense meditation and the hours of silence and physical restraint had led to a volley of daydreams. “But all of it had the hero-warrior archetype,” Novogratz said. “The archetype I grew up with. And it got to be cartoony at times. Jesus fucking Christ, dude, I saved the plane. Or saved the woman from being harmed. Or, you know, re-created the way Robin Hood”—a philanthropy co-founded by Paul Tudor Jones—“should raise money. Or ran for office. Or made more money on Ethereum so I can donate more. I was, like, Man, how big is your fucking ego? I got probably four years of daydreams or thought process in eleven days.”

A few weeks after our lunch, in the height of the summer, we were standing on a makeshift dock in the Bronx watching black men in shackles and orange jumpsuits board the Vernon C. Bain Center, a barge brought up from New Orleans to serve as a jail and a New York City Department of Corrections intake-and-processing center for the borough. “The boat is symbolic,” Novogratz said. “It’s a slave ship.” Cheap black shoes nicknamed Patakis, for the former New York governor, who was in office when they were first distributed, were strewn around. Released detainees get rid of them as a sign of their new freedom. An employee of the Bail Project, a young Yale graduate, was posting bail for two detainees on the boat. Novogratz is the chairman of the Bail Project’s board and its principal contributor. His daughter Anna encouraged his interest in the fund after working for the Bronx Defenders, a nonprofit legal-services group. The project’s mission is simple: to provide bail for detainees, who often cannot afford even small amounts and get trapped in the system.

On the boat, a clerk told a middle-aged Latina that she needed twenty-five thousand dollars instead of twenty-five hundred in order to bail out her son. Apparently, there had been a computer error. “They keep sending me back and forth,” the woman said. Her son suffered from multiple sclerosis. “He can’t pick up his hand, his face twitches. His muscles don’t work with this weather.” Her case was not being handled by the Bail Project, and it appeared that her disabled son would remain on the jail boat.

“The Bail Project is a radical move in its own right,” Novogratz said. “It’s a huge fuck-you to the system. We know the first three to five days in jail are the most damaging.” He listed sexual assault, job loss, suicide, and lost places in homeless shelters as potential outcomes.

Anthony Romero, the head of the American Civil Liberties Union, which has received substantial funding from Novogratz, told me, “A lot of hedge-fund-investor types are mostly thinking about throughputs and R.O.I.”—return on investment. “He has a better appreciation of the nuance of trying to tackle social issues.”

Novogratz thinks about philanthropy more than any other financier I met during the course of my research. As a result, spending time with him means witnessing the near sum total of New York’s fund-raisers. Some of them take place in the Novogratzes’ vast Tribeca apartment (joining Robert De Niro’s former duplex and Harvey Keitel’s former one-story pad). Here one could see the singer Cassandra Wilson at a fund-raiser for the Jazz Foundation of America, as the Puerto Rican musician Joe Quijano shyly watched the festivities from his wheelchair. On another night, a dinner in a hotel ballroom was accompanied by a video procession of parents explaining how they were bankrupted by their children’s cancer diagnoses. On another day, Novogratz hovered over Times Square on a digital billboard as he introduced a wrestling tournament between Japan and the United States to benefit his charity Beat the Streets, which uses wrestling to help at-risk kids.

It is hard not to think that in a fundamentally humane society none of this glittering largesse would even be necessary—that inner-city kids would get proper schooling, elderly jazz musicians would have hot meals and shelter, young people in the Bronx who have committed minor nuisance crimes would not be locked up on repurposed jail barges, the parents of children stricken with near death sentences would not be forced to declare bankruptcy. Novogratz, who considers himself “halfway between center-left and progressive,” would probably agree. During my lunch with him at the Mercer Kitchen, he told me, “I’ve always said I’d run for office if I had a five-year period in my life where really I felt, like, Hey, my behavior is laudable.” He laughed. “That I haven’t done stuff that would embarrass myself, or my kids, or my family, or my parents. Maybe I’ve got two months’ traction on that in the past.”

By the fall, Novogratz was a billionaire once more. The price of a single bitcoin had been close to three thousand dollars during the summer; now it was clawing at five thousand. I visited him one Wednesday in October, at his office, walking in past a large statue of Evel Knievel in the lobby—the base reads “Bones heal, pain is temporary and chicks dig scars.” Plush sofas were occupied by representatives of the Brown University endowment, a member of the board of Tesla, and the heads of a major publicity firm, among others.

Two weeks earlier, Novogratz had announced his decision to rejoin the hedge-fund world and launch a cryptocurrency fund with a hundred and fifty million dollars of the money he had personally made on crypto and three hundred and fifty million from outside investors. (Boaz Weinstein, who is the founder of the hedge fund Saba Capital Management and also a former classmate of mine at Stuyvesant, told me, “I like his tactic: ‘It’s a bubble! Ride the rocket, baby!’ ”) Novogratz gathered some members of his staff to discuss the emerging fund. Most were dressed casually, in sweatshirts and jeans. Novogratz typically wears T-shirts that read “Coach” or “Clam Bar” and his favorite speed-racer pants, and today he was dressed in similar regalia. “I want to raise money as fast as we can,” he said. “I have a foreboding feeling markets are going to be a lot higher in six months.”

He continued, “When you meet with people, you’re doing the same dog-and-pony show—it’s boring. I want to bring someone who has a different skill set than me, someone who’s younger and smarter. At Pantera”—an established fund—“they rolled out a teen-ager. He was giving out odds on bitcoin code being cracked.” Novogratz smiled. “I’m feeling like a California V.C.!” he said.

“How much have we spent on alcohol?” a woman asked. “Three thousand seven hundred?” Novogratz threw a raucous crypto party every Wednesday night, describing it as the cantina scene in the original “Star Wars.” In George Lucas’s universe, Novogratz would presumably play the role of resident Yoda by dint of age and stature. In an effort to maintain standards, a motion to ban bankers in suits was passed (often, it is hard to figure out whether Novogratz’s bro culture is co-opting the crypto-geeks or it’s the other way around) before the staffers dispersed.

After that discussion concluded, the meetings started. Novogratz has a desk in his office, but I’ve rarely seen him behind it. He prefers his couch, sometimes adjudicating disputes from it like a don, sometimes sprawled across it with his reading glasses on, a sliver of belly visible beneath a T-shirt. Among Novogratz’s favorite phrases are “It’s above my pay grade” and “I’m going to grab one of my geeks.”

“I’m a decent leader, but I’m not a manager,” he later told me. “A leader has to be inspirational. A manager has to stay in the lane.”

Two well-tanned publicists, a woman and a man, came in with an idea for a gender-specific coin. “A lot of women don’t understand finance,” the woman said, pitching a concept she was calling Y-Coin.

After they left, I asked Novogratz what he thought. He shook his head.

A thick-bearded producer in a black hat and a tuxedo jacket came in to discuss a film that Novogratz was producing. He has been in the film business since leaving Fortress, and recently funded the under-the-radar, oddly mesmerizing “My Friend Dahmer,” a film about the early years of the serial killer. He was now staking some of his crypto wealth on a more commercial project, called “Assassination Nation,” a thriller written and directed by Sam Levinson.

“If we don’t get into Sundance—” the producer started to say.

“We’re fucked,” Novogratz finished. (The film did get into Sundance.)

A fresh-faced young man with Fordham and Citibank on his résumé came in. “Did you play sports?” Novogratz asked right away.

“Ice hockey.”

“What’s the worst morally shitty investment you ever did?”

“Payday-lending stuff.”

“We’re rich enough not to have to do shitty things.”

“I knew I was going to get shit for wearing a suit,” the young man said, to Novogratz’s laughter.

“I’m fifty-two,” Novogratz told him. “I can probably still beat you in a wrestling match. My knees are the only problem.”

At 6 P.M., the cantina was in full swing in a large back office, with idealistic young people presenting me with an endless array of uses for the new technology, including some kind of medical or pharmaceutical blockchain scheme and a “smart fabric” company that is launching its own token. “My white paper is in your possession!” a man with a Slavic accent yelled at Novogratz. “If my guy says yes, I’ll do it,” Novogratz yelled back.

After we left the party, Novogratz told me, “My role is spokesperson and adult. They’re all young and they could use some guidance.” His message to the youth making millions in the (currently) underregulated crypto space: “Pay your taxes!”

Cryptocurrency has been compared to the seventeenth-century Dutch tulip mania, when tulip bulbs sold at outrageous prices, completely divorced from their intrinsic value, until the market inevitably collapsed. Crypto’s “tulip camp” includes a variety of investors and thinkers, among them Warren Buffett and JPMorgan Chase’s C.E.O., Jamie Dimon. One of Wall Street’s so-called “permabears,” the economist Nouriel Roubini, has predicted that bitcoin eventually will crash to zero. “There is no there there,” Aswath Damodaran, a noted expert on valuation at N.Y.U.’s Stern School of Business, told me. “I don’t think that there has been so much ink spilled, so much talk generated, and so much analysis done of so little in the history of markets as I have seen in the last two years on cryptocurrencies.”

After bitcoin and other currencies soared over the summer and fall, Novogratz presented this stage of crypto as a “speculative mania phase” that would crash like the dot-com bust but then reëmerge with more mature players. Out with AltaVista, in with Google. In Novogratz’s estimation, individual cryptocurrencies would fail—although he is bullish on bitcoin and ether retaining their value in the long term. “I don’t know if the speculative phase ends in March, ends in a year from now, eighteen months from now,” Novogratz told me, “but it will end.” He suggested that it will end when “too many people have bought in.” (At a dinner during the fall of 2017, one of my favorite Oberlin professors, a Marxist, told me that he had just bought some ether.)

I asked Jed McCaleb, a founder of the popular cryptocurrencies ripple and stellar, whether the financial industry has been too late to the party. “Not too late—too early,” he said. “It’s still pretty early, technically. There’s a hype preceding the reality similar to what you saw in the dot-com bubble. There are lots of good ideas but lots of nonsense that doesn’t warrant the kind of money that’s been dumped in it. A lot of investors don’t know which is which.” I asked him if he thought Novogratz knew. “It’s easy to look smart in a bull market,” McCaleb told me, “which is not to say he’s not a smart guy.”

A friend who works in finance once told me, “Nobody survives a billion.” From my own research, I’ve found that immense wealth often leads to regrettable personal and business decisions. Novogratz’s billionaire survival tactic seems to be a blend of excessive personal spending, over-the-top philanthropy, and meditation.

In November of 2017, I went to Tamil Nadu, India, to meet Novogratz’s spiritual guru, Krishnaji, at his meditation academy. Krishnaji, a handsome man smelling of good soap, has imparted to Novogratz his philosophy of acknowledging and dissolving the “suffering state” and living his life from what he called “the beautiful state.” (I kept thinking of his philosophy as “the two-state solution.”) Krishnaji and Novogratz travelled across India in January of 2015, looking for distressed properties owned by India’s Central Bank in which to invest. During the trip, Novogratz told me, all he wanted was to meditate with Krishnaji, while all his business-minded guru wanted to do was work on their private-equity deals. “In the next seven years we’ll package the property, developing it, making it plots and lots, depending on where the land is situated,” Krishnaji explained when I met him in November.

The Web site for Krishnaji’s real-estate ventures, White Lotus Structures, declares that “a palpable touch of the sacred is experienced in all its creations.” (“He’s a piece of work,” Sukey Novogratz told me, when I brought up his business dealings. Krishnaji, for his part, told me that he pumps a lot of money back into the academy.)

As I walked down the frangipani-strewn “Silent Path” that connected my villa with the beach on the Bay of Bengal, one of the academy’s gurus told me that Krishnaji “does various businesses from a beautiful state of being. That is the reason for his success.”

Yet Krishnaji was straightforward when it came to Novogratz’s departure from Fortress: “He saw that throughout his life he’s had this image of himself as a great financial genius, and that, in that particular incident, he had made such a huge blunder that his image was shaken. He was not a financial genius at that moment—it was a stupid decision he had made. He saw that his suffering was not so much the loss of money, because he could again make it back. His suffering was actually the death of an identity.”

Novogratz’s cryptocurrency hedge fund never launched. In December, after the price of a single bitcoin rocketed to more than nineteen thousand dollars, Novogratz told me that “it would be a different proposition raising a crypto hedge fund today than it was three months ago.” He said he was not comfortable running other people’s money when the currency was at its peak, and predicted that bitcoin would consolidate at between eight and sixteen thousand dollars. “I’d rather look stupid than be stupid,” he added. Right after he told me of his plans to shelve his hedge fund, bitcoin experienced one of its habitual micro-crashes, falling to under fourteen thousand dollars a coin.

Some people thought that Novogratz had simply not raised enough capital to launch the fund. Others focussed on the fact that, despite his penchant for showmanship, he was not making a good case for his fund. “To build a fund, you need a lot of focus and attention to detail and have ambition to be institutional,” the manager who’d proclaimed Novogratz a mere salesman told me. “A great trade is not a fund.”

Before he bailed, Novogratz had described another idea to me, one several magnitudes more audacious—certainly more institutional, and potentially more durable—than a mere half-a-billion-dollar hedge fund. He wanted to launch a publicly traded merchant bank solely for cryptocurrencies, which, with characteristic immodesty, he described as “the Goldman Sachs of crypto,” and was calling Galaxy Digital. “I’m either going to look like a genius or an idiot,” he said.

Novogratz announced the bank’s launch in early January, the same week that Dimon, of JPMorgan Chase, who is one of the most vocal critics of cryptocurrency, publicly regretted calling bitcoin a fraud (“The blockchain is real,” he told Fox Business). Shortly afterward, I sat down with Novogratz in his Tribeca apartment’s far-flung kitchen to discuss Galaxy Digital.

“Goldman Sachs can make money if the stock market goes up and if the stock market goes down,” Novogratz said. “That’s what we’re trying to build. Right now, we’re still going to be way correlated to the way the market goes for at least the first year or two,” he conceded. “But we’re trying to build enough diversity into the business that we can withstand hurricanes.” He told me that Galaxy Digital would combine his considerable crypto holdings with an asset-management operation, a trading business, a venture that would invest in new initial coin offerings, and an advisory arm that would counsel companies.

The new entity’s launch was not so much an I.P.O. as a complex R.T.O., or reverse takeover, involving a Canadian shell company called Bradmer Pharmaceuticals. Galaxy Digital would still be based in New York, but because Canada offered easier and faster access to the public market Novogratz had decided to launch on the Canadian TSX venture exchange, with plans to eventually transfer to Canada’s main exchange. He would contribute around three hundred and fifty million dollars, while raising another two hundred and fifty million dollars.

“It’s a brilliant move,” Josh Brown, the C.E.O. of Ritholtz Wealth Management, in New York, said. “It’s always better to own the casino than to play.” The hedge-fund manager Jeff Gramm told me, “If you really believe in crypto, this is an opportunity to dominate a growing niche that Goldman Sachs and the other big banks might be too risk-averse to bother with. Even if ninety per cent of these cryptos are total bullshit, you could build a really nice business. Think about Michael Milken and Drexel Burnham in the late seventies and early eighties. None of the big investment banks wanted to touch high-yield trading, and Drexel ultimately became the most profitable bank on Wall Street.” (Milken, known at the time as the “junk-bond king,” was also sentenced to ten years in prison for securities fraud. He was released after two years. Novogratz has publicly appealed to cryptocurrency tycoons to play by the rules and avoid Milken-like fates.)

Jed McCaleb, of ripple and stellar, predicted that in the next couple of years a lot of crypto companies with big balance sheets will acquire one another. “A merchant bank can facilitate that,” he told me. “It’s a timely thing to do.”

Of course, not everyone is on board with the idea of a finance billionaire Goldmanizing the new space. A self-described “crypto lawyer” wrote on Twitter, “Hey I know—let’s use crypto to recreate precisely the fucked up institutional structures that crypto was created to surpass.”

Recently, Novogratz showed up at a staid dinner for retired Goldman Sachs partners wearing his speed-racer pants. He had attended these dinners before, but not from his current position of success in crypto. The prodigal son had returned. The investment bank—encapsulating the highs and lows of his career—finds its way into many of his conversations. “We hired Goldman’s best guy in blockchain,” Novogratz told me on several occasions.

Government regulation remains the greatest challenge to the future of cryptocurrency. “It’s stressful, because the regulatory environment’s not clear,” Novogratz said. “You don’t even know what the rules are. In every country. Even in the U.S.”

On the day we met at his apartment, a regulatory crackdown in China, preceded by one announced in South Korea, was pushing the price of bitcoin down. (It hasn’t returned to its December high, and is currently priced at around seven thousand dollars.) Meanwhile, it appeared that hedge funds, many of which had ended 2016 either ailing or dead, were reporting their best returns in years. After six years of exploring finance, I concluded that, despite the expertise and the intelligence on display, nobody really knows anything. “In two years, this will be a big business,” Novogratz said, of Galaxy Digital. “Or it won’t be.”

His attitude seems to come from a battle-hardened place. “You know, when you’ve screwed up as much as me in life, you’re not so worried about it,” he said, over a glass of fine Burgundy, his voice echoing across his palatial kitchen. “I’ve tried my best. I think I’m right on this thing.” ♦

This article appears in the print edition of the April 16, 2018, issue, with the headline “One Good Bet.”